


First Time

by Animekath



Category: Red Dead Redemption (Video Games)
Genre: Aftercare, Cunnilingus, F/M, First Time, Fluff, Fluff and Smut, Riding, Vanilla, fingers - Freeform
Language: English
Status: Completed
Published: 2019-06-07
Updated: 2019-06-07
Packaged: 2020-04-12 07:49:10
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 2,953
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/19127704
Author URL: https://archiveofourown.org/users/Animekath/pseuds/Animekath
Summary: Your first time with some cowboys and sweet aftercare.





	First Time

**Author's Note:**

> Hey Guys, Kat here!
> 
> Hey, hey, do you want to lose your virginity to some cowboys!? Well, here you go! *rolls around* I thought it would be interesting to write and also to see some soft boys treating you well!
> 
> I hope you enjoy it! Sorry for spelling and grammar!

##  **Charles Smith**

Foreplay with Charles lasted a long time, maybe over an hour, but he said you needed it. He wanted you to be comfortable as possible, experience each other's bodies with hands, lips and teeth. But Charles worried about hurting you since he knew he was a bigger size than most men, even women who were experienced struggled with his size. Charles would use his fingers and mouth on your pussy, stretching you nice and Vast for him, loving the delightful moans coming from your lips.

“C-Charles, ple-Mm...I’m ready.” You whimpered out, your fingers running through his hair as his tongue licked your clit.

“You sure?” Charles asked, raising his head to look up at your heated state. You nod your head, Charles seeing the pleading look in your eyes. “Okay.” He pulled back and brought you onto his lap, his back resting against the pillows. He held his cock steady for you, his dark tip running along your slit. “Lower yourself onto me. Take your time, Hummingbird.” He said softly, kissing your forehead.

You placed your hands on his strong shoulders, letting out a shaken breath as you lowered yourself. Charles let out a small groan as he felt his cock sliding inside your tight pussy. “Easy, Bird...You don’t need to take all of me.” He breathed out. You didn’t take all of him at first, taking half of his shaft to get used to the feeling. Charles had to admit to himself that he loved how tight you were, flattered to be your first time and that you trusted enough for him to take it.

He would rub your clit slowly so you could ease into it, loving when you moaned out his name or grip his shoulders. After a while, you built enough confidence to lower yourself more and more until he was entirely inside you. “Ah-!” You gasped, hugging him close when you felt his cock hitting your womb, Charles took back by your actions.

“Shhh...It’ll get better, I promise. You are doing so well.” Charles said in a calming tone as his hand ran along your back.

It felt good indeed, although you were sore the next morning, but Charles ran you a bath and told you to rest for the day.

##  **Bill Williamson**

Bill was anxious at first, not wanting to make you uncomfortable or hurt you. He forgot the last time he was with a virgin woman to know what to do, but there was something he thought would help...Just eat the hell out of you.

You rest back on the bed with your legs open, your fingers running through Bill’s hair as he ate you out. It felt oddly good at first, and you didn’t want Bill to stop, feeling his thick fingers curl up inside your pussy. “B-Bill...” You moaned out, your free hand gripping the bed underneath you. “So good...Nnh.” You bit your lip as he continued. You would bite your lip when his beard brushed up against your thighs, having no idea if it was pleasing or ticklish. “Please...More.”

Bill pulled his head away, licking his lips before wiping his mouth clean. “I will don’t ya worry.” He breathed out; his cheeks tinted red. He towered over you as he went between your legs, rubbing his cock along your slit. “Ready?” You nod in reply before feeling him slip inside, going slow so you could ease into it. You held onto his strong arms, letting out a shaken moan as he stretched you out. “How does it feel?”

“U-Uncomfortable and...Full. but it doesn’t hurt.” You breathed out, giving him a reinsuring smile so he would relax his worries. Bill moved steadily so you could get used to the feeling, moaning every time he slipped in. His might be below average size, but his shaft felt thick, opening you nice and wide for his cock.

You were sore the next morning, but you and Bill stayed in bed, resting against his hairy chest as his hand rubbed your lower back lazily. You just slept there for hours, enjoying each other's embrace.

##  **Hosea Matthews**

It was obvious that Hosea had a lot more experience than you, knowing how to please a woman and make her putty in seconds. He was slow with you, seeming to enjoy touching every part of your body and teasing a few times. But he always asked if you wanted this since he was much older than you, questioning if you wanted someone younger then himself. You always pulled him into a passionate kiss, saying you wanted him and no one else. It made the older man happy, but he still had his doubts.

You would sit on his lap as his fingers got to work, stretching and curling inside you, knowing which areas to rub and graze over with his skilled fingers. “You’re soaking my pants, Sweetheart. You must be enjoying this.” He grinned, feeling your body heated by his words. He placed kisses along your bare neck, nibbling and sucking to leave small marks on your skin. His free hand would trace your curves and go up to your chest to rub your perked nipples.

“H-Hosea...” You whimpered out, practically grinding yourself onto his hand as he continued to pleasure your body. “Please, I...I’m ready.” You said softly.

“You sure?” He asked as he looked up at you, pulling his fingers out of your pussy. He placed you on the bed, now over your body with his cock against your opening. “You ready? Because this is it, you know?”

You reached out to cup his cheek, giving him a reassuring smile. “Hosea...I want you so much...I am not going to regret this. Please, Hosea. Take me.” His eyes softened at your kind words, his heart swelling in his chest. “Ah...” You whimpered as he penetrated you, his cock pretty long but thin, nearly hitting your womb. “Fuck...” Hosea took it slow, waiting for you to tell him to stop his actions but you didn’t, making him relax. He would kiss and touch your body as he took you, wanting you to feel as much pleasure as possible.

The next morning you woke up by the smell of coffee and breakfast, Hosea softly petting your head as he read his newspaper. He said you could go to town together to get you both cleaned up and buy you something pretty.

##  **Dutch Van Der Linde**

Dutch did it a bit differently then you thought. He rested back and let you touch his body as you pleased, maybe to comfort you or to see how you would touch him. You took off his clothes and felt up his chest, loving the hairs against your hands and feeling his muscles against your touch. Dutch hummed as he watched your hand lower, his own hands taking off your clothes. “You okay there, Darlin’?” He asked in a low tone, feeling your heat against his hands.

“Yes...Just nervous.” You muttered, giving him a small smile. Your hand palmed on his tented cock, the man letting out a deep groan which made your body shiver. You undid his pants and took out his cock, biting your lip as you touched the base, feeling Dutch twitch and throb. “Fuck...You’re so...”

“Yes? Use your words, Darlin’.” He hummed, his hand going between your legs to run along your clit which made you gasp.

“B...Big and...Hot.” You breathed out, your hips moving on their own as he continued to touch you, his middle fingers slipping inside your pussy. “Mmm...” You rest your head against his shoulder as you both continued to touch each other, Dutch’s breathing was deep against your neck. It continued for a while, Dutch spreading your walls with his fingers and rubbing your clit, before pulling them out to replace it with his cock.

“Ready?” You nod your head at his question. He placed his hands on your hips before lowering you down, moaning as he was now entirely inside you. He felt average but seemed to have a thick base, stretching you out wide for his cock to be snug inside your pussy. “Shhh, there you go, sweetheart. Oh, you are doin’ so well, aren't you?” He purred, watching his cock inside you. “Mmm...You are squeezin’ around my cock. Fuck...I love it.” He grinned, kissing along your neck before he let you move your hips at your own pace. Dutch would watch you ride him but gave the odd thrust up to make you cry out, loving how you moaned out his name.

The next morning, you felt sore and your legs aching, but Dutch was there for you. He gave you some coffee and then grabbed a washcloth to get rid of the mess between your legs, telling you what a good girl you are.

##  **Kieran Duffy**

Kieran was a blushing mess as both of you were naked together, being gentle and caring for you. He always asked if you were okay, wondering if he was hurting you and would mumble a sorry when you twitch. Kieran didn’t want to hurt you or make you uncomfortable. He wanted your first time to be special. But he was so nervous that you had to be the one to comfort him, telling him it was okay and that you trusted him.

“Kieran, fuck.” You breathed out, feeling his fingers curl up and pump inside you as your hand pumped his cock. The poor boy rested his head on your shoulder, taking short breaths, moaning when your thumb rubbed his red tip. You didn’t know if you should be nervous or flattered that you got Kieran like this. “S-So good...Nh...Take me, Kieran.”

He pulled his head away, resting his forehead on yours. “Really? You sure?” You nod. He pulled his fingers out and leaned you back on the bed, going between you legs so he could get in position. “ready?”

You giggled softly, nodding your head. “Yes, Kieran. No need to be nervous, I want this.” You smile up at him, cupping his cheek. “Shouldn’t it be me being nervous about this since it's my first time?” You questioned teasingly, his face redden. You knew Kieran wouldn’t hurt you, though, you trusted him. “Ah...” You whimpered as he slipped inside your pussy, his cock thin but long inside you. “Kieran...”

He took it slow with you, always asking if you were comfortable and wanted to stop. At some point, you got on top to ride him so he would understand that you wanted this. Kieran became putty underneath you, moaning your name and saying the dirtiest stuff when he got into it, bucking up into you to go deeper.

When you woke up the next morning, Kieran was not there, making you question where he went. But it wasn't long before he came back, holding a bunch of flowers for you which he picked himself. He was too cute for his own good.

##  **Javier Escuella**

Javier knew how to treat and pleasure a lady; everyone knew that. But when he knew it was your first time, he was a hell of a lot gentler. He would butterfly kiss your skin as his hands traced over the curves of your body, muttering sweet words to you. His head went between your legs as well, licking and sucking your clit as his fingers stretched and rubbed your walls to prepare you. You reach out to touch Javier, but he would stop you, saying it was your night to be pleased, his time will come in the future.

“Mierda...You taste so fuckin’ sweet.” Javier groaned out against you, continuing to eat out your pussy with his tongue slipping between your folds to get a good taste of you. You whimpered by his actions, your fingers running through his loose hair. “I can do this all night.”

“P-Please, Javier. Any more and I’ll climax.” You breathed out, looking down at him. “I’m ready...Please, Javier.” Javier pulled out, licking his lips as he smiled down at you. “Por Favor.” He hummed at that and smiled, pulling you into a kiss, but it made you pout. “Ew, I’m all over your face.” Javier laughed at that and shook his head, finding you so adorable.

He lifted you on his lap, hugging your waist with his cock rubbing up against you. “Ready?” You nod, kissing his forehead. Javier slowly slipped inside you, both of you moaning at the pressure between. His felt average but his tip was thick. With his size, he knew how to use it very well to make a woman go crazy.

Javier hugged your waist as he took you, loving when you moaned into his ear and begged him to go faster. He would ask once in a while if you were okay and felt comfortable, your reply always being a loving moan.

The next morning, you have woken to see a plate of food beside you and Javier playing his guitar. You scooted over to rest beside him as you ate, a small smile going on his face.

##  **Arthur Morgan**

For a man who was dangerous and looked intimidating, he was a soft giant with you. He took his time with you, kissing along your neck as his large hands touched your naked body. He would say soothing things into your ear to know that you were safe with him, that if you wanted to stop then tell him. He was behind your naked body while his hand palmed your breast and the other cupped your pussy, his thick fingers pumping inside you.

“That’s my girl...Just relax. I got ya.” He whispered into your ear, placing kissing along your neck. “Yer doin’ such a good job for me. Fuck, yer pussy is squeezin’ my fingers.” He groaned, your body shaking at his deep voice. “Ya okay?”

“Y-Yes, Arthur. You are just so good.” You gasped when he pinched your nipple, a grin on his lips when you pouted. “Meanie.” You bucked up into his hand as he curled them up inside you again. “Arthur, please. I want you...” He nodded, pulling his fingers out and cleaned them with his mouth, groaning as he tasted your juices on his tongue. He rested you on the edge of the bed, one leg on the bed while the other went over his shoulder. He rubbed his cock against your slit, groaning at how wet you were for him.

“Fuck...” He groaned as he eased in, watching you body shutter by his size. His cock was above average and was thick on the base, stretching you out to your limit. “Shit, Darlin’. Ya okay?” He asked as he was inside. You nod your head but looked a bit uncomfortable. “It’ll get better, I promise.” He hummed out, staying inside you until your walls eased around him.

Arthur took you gently, going slow until you wanted to speed up, his thumb going to your clit to make you moan louder for him. He would lean over to mark your neck, to ease you but also to let people know that you were his girl.

When you woke up the next morning, Arthur was still asleep beside you, his strong arm around your waist to keep you close to his chest. You watched him for a while before he woke up, placing sweet kisses on your body and telling you what a good girl you were.

##  **John Marston**

John may look like a doom and gloom guy, but he would quickly get flustered with you, especially when you wanted him to be your first. He was stiff at the beginning but eased into it when you kissed along his neck while your hand nervously palmed his cock. He strips you from your clothes and then himself, so you were bare against each other as you kissed.

He placed you onto the bed and grunted when you parted your legs for him to see. “Damn...” He bit his lip. “Can...Can you please touch yourself for me?” He asked softly, seeing the flustered look on your face but agreed anyway. John slowly pumped his cock as he watched you finger yourself, loving your moans and you getting nervous by him watching you. “That’s it, girl...You look so beautiful.” He grunted, his thumb rubbing along his tip. “Nngh...”

“J-John...” You whimpered out as your fingers pumped inside you, stretching you out for him. After a few more strokes and stretches, you parted your walls for John. “Please...” The man bit his cut lip as when you did that, going between your legs.

“Just...Tell me if it’s too much.” John grunted out before grabbing your hips, now easing himself in. You gripped onto his arms when he was inside, his cock Above average and slim inside you. “Fuck...” He groaned out, grasping onto your waist. “Your cunt feels so good.” You wrapped his arms around his neck to bring him close for a kiss.

It was clunky at first, but when you both got into it, it felt so good. John would kiss and bite along your neck to leave marks, while your nails dug into his back to leave scratches. John would whisper into your ear to tell you how good you felt, and begged to come inside you.

The next morning, you have woken up with John passed out on his stomach, looking so cute in his sleep. You giggled as you got up, cleaning yourself up and got ready to get some coffee. You woke John up with kisses all over his face and some fresh coffee.

THE END! <33


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